25 Lessons at 25

June 29, 2024

I turned 25 recently. Here are 25 lessons I’ve learned along the way.

1. Sprint towards hard conversations.

It’s rarely as bad as you think it will be, but it only worsens with time. Clear is kind.

2. On a relative basis, very few people care about you. Cherish the ones who do, and stop worrying about the others.

The percentage of people in your life who spend meaningful time thinking about you rounds to zero. This is a gift. Find the special ones and stop giving the others so much energy.

3. Find a partner who pushes you to improve while also supporting who you are at your core.

If you want to be excellent at what you do, you need a support system for the other parts of your life. There’s nothing better than a great partner who just gets it. (👋 Rhegan)

4. Adjust your communication based on the listener.

Still working on this one, admittedly, but if your goal is to persuade, then reframe the message in a way that will land for your audience. Your personal communication preferences don’t matter in this situation. (Identifying what lands for someone is a skill in itself)

5. All meaningful change begins with good storytelling.

In a world where generating content is cheap and ideas are easily repeated, you win by moving people. You win if you can make someone feel excited, fearful, anxious, or emotional with your words.

6. Learn to love public speaking; it’s the most effective tool for storytelling.

Limiting your storytelling to only writing is playing in hard mode. Tone, body language, and presence matter way more than most think, and these muscles atrophy if not practiced consistently.

7. Trust gets built over years and destroyed in seconds.

Build your reputation carefully and intentionally, and don’t make dumb decisions that ruin that hard work.

8. Everything (everything!) is learnable.

All knowledge in the world was discovered, learned, and taught. There is no magic formula; you just have to do the work.

9. Budget your energy just like your money.

Energy vampires exist, and they will not be satisfied until you have nothing left to give. Avoid these people and figure out how to recharge.

10. Working hard is good.

Hot take (?) - it’s good to work unreasonably hard at the thing that sets you on fire. Way fewer people do this than you would think! Even going slightly above and beyond is a huge competitive advantage.

11. Sometimes, the only way out is through.

Keep going and stay in the game. Sometimes, the way to win is to just put your head down and move forward. It might not be fair that you’re in that situation, but that doesn’t change how you get out of it.

12. Be embarrassed of who you were a year ago and learn from it.

How will I feel about this blog post when I’m 26? Hopefully, at least a little embarrassed - continuous improvement is a gift.

13. Pay it forward at every opportunity, even when you feel like you don’t have anything to pay.

You don’t need money, status, or much time to help others. Remember those who did it for you and choose to be that person for someone else.

14. On the long arc, kindness wins.

Do not get involved in drama at the expense of others. This includes bartering with other people’s information - there are better ways to build up trust and social stature in your network. It never ends well, and the universe pays attention (karma is real, and it will come back).

15. It’s not over until it’s over.

Don’t prematurely celebrate - wait for the money to hit your account, the Docusign to close, etc. The universe has a habit of cruelly punishing you for getting ahead of yourself.

16. Pour your time into something that sets the world on fire.

I have the Jesuits and Boston College to thank for this one.

17. You can’t outsource your personal growth.

Find people who can help, but don’t expect them to do the hard work for you. It’s your responsibility alone to improve and become a better partner, leader, friend, etc.

18. Figure out what habits lead to clear thought and lean in on those.

Or, figure out when you feel the worst mentally and do the opposite of that. Either way, create an environment where your brain can win and do its job.

19. Fear is natural but is (usually) wasted energy.

Easier said than done, of course. Figure out how to separate fear that is teaching you something from fear that is lying to you.

20. Have more meals with friends.

I can’t think of a single time I regretted making time to eat with friends. Do this more often - over the long run, the money/time/calories won’t matter, but the energy and relationships will.

21. Different people for different seasons in life and business.

It’s ok to shift the people around you as you grow and change. Just be intentional, lest you wake up one day and realize the wrong people are on the journey.

22. Pursuing the truth is time well spent.

Dig until you reach the core, and don’t be afraid to change your mind.

23. Re-underwrite your beliefs with new evidence.

Changing your mind is a good thing. New evidence that challenges a belief feels uncomfortable, but it is critical for seeking the truth.

24. Don’t say or put things in writing you don’t want to be read in court, by investors, or in front of your family.

Enough said.

25. You usually need far fewer resources than you think to go far.

The human spirit is indomitable. You will figure it out.